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.Dd $Mdocdate: October 1 2014 $
.Dt STARTTLS 8
.Os
.Sh NAME
.Nm starttls
.Nd ESMTP over TLS/SSL
.Sh DESCRIPTION
STARTTLS is an ESMTP option, defined in RFC 3207, which is used to conduct
ESMTP transactions over TLS circuits.
This is used to increase the security of mail server transactions.
.Pp
STARTTLS allows for the combination of several security solutions for MTA
(mail transport agent) level services through the TLS suite.
These security features include:
.Bl -tag -width Ds
.It Confidentiality
Encryption is used to protect data from passive monitoring.
An attacker would have to recover the encryption key used to
decode the transmitted data.
.It Integrity
Hash algorithms are used to ensure the integrity of the
transmitted data, and alternatively the timestamp, protecting against a
replay attack.
This protects data from modification in transit.
.It Authentication
The use of public key encryption allows for the strong authentication of
either, or both, communicating parties.
This can be used to allow for select features, such as relaying,
to be controlled more securely.
.El
.Pp
A new ESMTP option, STARTTLS, has been added.
This is presented by the server when an ESMTP session is initiated.
The client then begins the TLS portion of the ESMTP session by issuing
the command
.Dq STARTTLS .
The remaining portion of the ESMTP session occurs over a TLS channel.
.Ss Creating a private key and certificate for an MTA
This example assumes you are creating your own self-signed certificates
for use with
.Xr smtpd 8
and STARTTLS.
If you have an existing private key and you simply wish to generate
a new certificate (for example, if your old certificate has expired),
see the section entitled
.Sx Creating a certificate with an existing private key .
.Pp
For the purposes of this example the certificates will be stored in
.Pa /etc/ssl ,
though it is possible to use a different directory if needed.
.Pp
Next, you must generate a
.Ar DSA
parameter set with a command like the following:
.Pp
.Dl # openssl dsaparam 1024 -out dsa1024.pem
.Pp
This would generate
.Ar DSA
parameters for 1024-bit
.Ar DSA
keys, and save them to the
file
.Pa dsa1024.pem .
.Pp
Once you have the
.Ar DSA
parameters generated, you can generate a certificate
and unencrypted private key using the command:
.Bd -literal -offset indent
# openssl req -x509 -nodes -days 365 -newkey dsa:dsa1024.pem \e
  -out /etc/ssl/mycert.pem -keyout /etc/ssl/private/mykey.pem
.Ed
.Pp
You may adjust the lifetime of the certificate via the
.Fl days
parameter (one year in this example).
.Pp
Make sure to leave the private key files unencrypted, using the
.Fl nodes
option.
Otherwise the MTA
will be unable to initiate TLS server functions.
.Pp
You can verify that the newly-generated certificate has correct information
with the following command:
.Pp
.Dl # openssl x509 -in /etc/ssl/mycert.pem -text
.Pp
If you don't intend to use TLS for authentication (and if you are using
self-signed certificates you probably don't) you can simply link
your new certificate to
.Pa CAcert.pem .
.Pp
.Dl # ln -s /etc/ssl/mycert.pem /etc/ssl/CAcert.pem
.Pp
If, on the other hand, you intend to use TLS for authentication
you should install your certificate authority bundle as
.Pa /etc/ssl/CAcert.pem .
.Pp
At this point, you no longer need the
.Pa dsa1024.pem
file and it can be removed.
.Pp
.Dl # rm dsa1024.pem
.Pp
Because the private key files are unencrypted,
MTAs
can be picky about using tight permissions on those files.
The certificate directory and the files therein should be
readable and writable only by the owner (root).
A simple way to ensure this is to run the following:
.Pp
.Dl # chmod -R go-rwx /etc/ssl/private
.Ss Creating a certificate with an existing private key
This example assumes you already have an existing private key,
.Pa /etc/ssl/private/mykey.pem .
You can generate a new certificate based on this key using the command:
.Bd -literal -offset indent
# openssl req -x509 -new -days 365 -key /etc/ssl/private/mykey.pem \e
  -out /etc/ssl/mycert.pem
# chmod 600 /etc/ssl/mycert.pem
.Ed
.Pp
You may adjust the lifetime of the certificate via the
.Fl days
parameter (one year in this example).
.Pp
After having installed the certificates
the mail server needs to be configured to accept TLS sessions.
For
.Xr smtpd 8 ,
it's as simple as adding a line like the following to
.Xr smtpd.conf 5 :
.Pp
.Dl listen on [...] tls
.Pp
After restarting the mail server, a new option should be presented for ESMTP
transactions, STARTTLS.
You can test this by connecting to the local host and issuing the
.Dq EHLO
command.
.Bd -literal -offset indent
# telnet localhost 25
Trying 127.0.0.1...
Connected to localhost.
Escape character is '^]'.
220 localhost ESMTP OpenSMTPD
EHLO localhost
.Ed
.Pp
After typing
.Em EHLO localhost
you should receive something like the following back.
.Bd -literal -offset indent
250-localhost Hello localhost [127.0.0.1], pleased to meet you
250-8BITMIME
250-ENHANCEDSTATUSCODES
250-SIZE 36700160
250-DSN
250-STARTTLS
250 HELP
.Ed
.Pp
You should see
.Dq STARTTLS
listed along with the other options.
If so, congratulations, the MTA will now use TLS to encrypt your mail
traffic when the remote server supports it.
If not, check
.Pa /var/log/maillog
to see whether the MTA has reported any security problems or other errors.
.Ss Uses for TLS equipped MTAs
The most obvious use of a cryptographically enabled MTA
is for confidentiality of the electronic mail transaction and the
integrity checking provided by the cipher suite.
All traffic between the two mail servers is encrypted, including the
sender and recipient addresses.
TLS also allows for authentication of either or both systems in the transaction.
.Pp
One use of public key cryptography is for strong authentication.
We can use this authentication to selectively relay clients, including
other mail servers and mobile clients like laptops.
However, there have been some problems getting some mail clients to work using
certificate-based authentication.
Note that your clients will have to generate certificates and have them
signed (for trust validation) by a CA (certificate authority) you also trust,
if you configure your server to do client certificate checking.
Two new entries are available for TLS options:
.Bl -tag -width Ds -offset indent
.It VERIFY
contains the status of the level of verification (held in the macro {verify})
.It ENCR
the strength of the encryption (in the macro {cipher_bits})
.El
.Pp
VERIFY can also accept the argument for {cipher_bits}.
Here are a few example entries that illustrate these features, and
the role based granularity as well:
.Pp
Require strong (256-bit) encryption for communication with this server:
.Pp
.Dl TLS_Srv:server1.example.net	ENCR:256
.Pp
For a TLS client,
require verification and a minimum of 128-bit encryption:
.Pp
.Dl TLS_Clt:desktop.example.net VERIFY:128
.Pp
Much more complicated access maps are possible, and error conditions (such
as permanent or temporary, PERM+ or TEMP+) can be set on the basis of
various criteria.
This allows you fine-grained control over the types of connections you
can allow.
.Pp
Note that it is unwise to force all SMTP clients to use TLS, as it is not
yet widespread.
The RFC document notes that publicly referenced SMTP servers, such as the
MX servers for a domain, must not refuse non-TLS connections.
However, restricted access SMTP servers, such as those for a corporate
intranet, can use TLS as an access control mechanism.
.Sh SEE ALSO
.Xr mail 1 ,
.Xr openssl 1 ,
.Xr smtpd 8 ,
.Xr ssl 8
.Sh STANDARDS
.Rs
.%A P. Hoffman
.%D February 2002
.%R RFC 3207
.%T SMTP Service Extension for Secure SMTP over Transport Layer Security
.Re
.Sh CAVEATS
One often forgotten limitation of using TLS on a mail server is the
payload of the mail message and the resulting security there.
Many virus and worm files are now distributed via electronic mail.
While the mail may be encrypted and the servers authenticated, the payload
can still be malicious.
The use of a good content protection program on the desktop is
therefore still of value even with TLS at the MTA level.
.Pp
Because TLS can only authenticate at the server level, true
end-to-end authentication of the mail message cannot be performed with
only the use of STARTLS on the server.
The use of S/MIME or PGP e-mail and trustworthy key hierarchies can guarantee
full confidentiality and integrity of the entire message path.
.Pp
Furthermore, if a mail message traverses more than just the starting and
ending servers, there is no way to control interactions between the intervening
mail servers, which may use non-secure connections.
This introduces a point of vulnerability in the chain.
.Pp
Additionally, SMTP over TLS is not yet widely implemented.
The standard, in fact, doesn't require it, leaving it only as an option, though
specific sites can configure their servers to force it for specific clients.
As such, it is difficult to foresee the widespread use of SMTP using TLS,
despite the fact that the standard is, at the date of this writing,
over two years old.
.Pp
Lastly, interoperability problems can appear between different implementations.
